Phenylacetylene → 1-Benzyl-4-phenyl-1,2,3-triazole

HRID 64498

Reaction equation

HRID 64498 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([N:16]=[N+:17]=[N-:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCl>[CH2:9]([N:16]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:18]=[N:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 10821PhenylacetyleneHCID 12152Benzyl azide

Product 1

HCID 113108941-Benzyl-4-phenyl-1,2,3-triazoleYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylacetylene (103 mg, 1.0 mmol, 1.0 eq.) and benzyl azide (133 mg, 1.0 mmol, 1.0 eq.) were dissolved in an air-tight lockable vial with a septum in 10 mL dry dichloromethane. The Cu complex (catalytic or stoichiometric amounts) was added, the vial sealed and the reaction stirred at room temperature for 2 days. For the removal of the catalyst complex the reaction mixture was put in 50 mL methanol and stirred for 20 min. The complex was removed by filtering and the filtrate was concentrated. Removal of the solvent and drying of the product in high vacuum resulted in the compound 1-benzyl-4-phenyl-1H-1,2,3-triazole as light yellow solid with 95% yield (245 mg, 0.95 mmol). The identity of the product was proven by NMR-spectroscopy, infrared spectroscopy and high-resolution mass spectroscopy.

Workup

  1. additionThe Cu complex (catalytic or stoichiometric amounts) was added
  2. customthe vial sealed
  3. customFor the removal of the catalyst complex the reaction mixture
  4. stirringstirred for 20 min
  5. customThe complex was removed
  6. filtrationby filtering
  7. concentrationthe filtrate was concentrated
  8. customRemoval of the solvent
  9. customdrying of the product in high vacuum

Sources & evidence

ORD record
ord-8b6831b1f2994bb4a02fe57cdc0f99b6
Source dataset
uspto-grants-2016_09
Patent number
US09447246B2

Linked notes

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